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Triethylamine → tert-butyl 2-carbamoyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

HRID 627016
ノート
印刷プレビュー

反応式

HRID 627016 の反応式
[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[CH2:10][CH:9]1[C:17]([O-:19])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].C(=O)(O)[O-].[NH4+].C[N:27](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.C([O-])(O)=O.[Na+].[OH-].[Na+]>[C:17]([CH:9]1[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[CH2:10]1)(=[O:19])[NH2:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8471TriethylamineHCID 14013Ammonium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118380491lithium 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

生成物 1

HCID 118380479tert-butyl 2-carbamoyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate
収率 102.7%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 14798Sodium Hydroxide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a suspension of lithium 1-(tert-butoxycarbonyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (100 mg, 370 μmol, Eq: 1.00) in DMF (5.00 mL) was added sequentially ammonium bicarbonate (90.0 mg, 1.14 mmol, Eq: 3.08), HATU (210 mg, 552 μmol, Eq: 1.49) and triethylamine (100 μL, 717 μmol, Eq: 1.94). The resulting dark yellow mixture was stirred at rt for 2 h. The reaction mixture was diluted with saturated aqueous NaHCO3 (10 mL) and 1 M aqueous NaOH (0.5 mL) and extracted with DCM. The combined organic layers were dried (Na2SO4) and concentrated in vacuo, using n-heptane to azeotrope off residual DMF. The resulting residue was purified by flash chromatography (silica gel, 12 g, 0% to 10% MeOH in DCM) to give tert-butyl 2-carbamoyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate as a white solid (100 mg), m/z=264 (M+H).

後処理

  1. extractionextracted with DCM
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by flash chromatography (silica gel, 12 g, 0% to 10% MeOH in DCM)

出典と根拠

ORDレコード
ord-918c9b286384419ca3f786afd28a077c
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309248B2

反応ノート

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